Apologies for the wall of text! I tried to format it to make it easier to skim or skip around. I’m new here, and want to be useful. The posting guidelines recommend specific things worth sharing, so in an attempt to make this organized and easy to read, I’m going to separate this out into different categories.

MINDSET:

  • It’s been an awkward amount of time since I’ve dated for a small variety of reasons, so I’m attempting to kickstart my love life a bit here. Pivotal for me has been reading Models (Mark Manson) and No More Mr. Nice Guy (I dunno. Google it). A universal refrain in those is that intimacy <- vulnerability <- honesty, which is a bit scary, but also super relieving. So, the mindset I was attempting to cultivate here was one where I’m not trying to impress, but to be honest, and just get to know her.

  • I got a bit caught up in the details of the date, and felt a decent amount of anxiety ahead of time. What if I plan something wrong? What if she doesn’t like what we’re doing? What if it’s not exiting enough? I texted a buddy, and he said, “You’re the badass sonabitch who is the good time. She should be lucky to have your attention for more than 2 seconds. So do what you have planned and just try and enjoy hanging out. Stop being a scared little bitch. Fucking pussywillow.” Haha.. That helped. But that’s the mindset I was able to maintain throughout the night. No pressure. We’re just getting to know each other. I’m a fun guy, and if she’s the right girl, she doesn’t need a perfect date anyhow.

LOGISTICS:

This is where I think I struggle the most. I asked for advice in a previous post, and got some helpful feedback. I think the flow of the night was really cool. Here’s what and when and why I did what I did:

  • I called her around 2:30 and asked when she’s free. She gave me a few days, and I asked what she was doing that (same) night, telling her I just wanted to do something low-key. Maybe that’s a no-no, but whatever.

  • I texted her to meet me at 8:07 at a specific part of the mall parking lot. I was a fre minutes late, unintentionally. When we got there, I told her we had two missions to accomplish but that I couldn’t tell her what they were.I’d previously told her that everybody looks better in glasses. She told me she didn’t. So, we went “shopping” for glasses for a while. We browsed for a while, then after that, I had her wait outside the candy store while I grabbed some thin mints.

  • By now it’s 9, and I take her to Barnes & Noble to buy hot chocolate. I put some thin mints in, and the game is how little can I add before she can guess what I’ve added. (This sounds weird and creepy as I type it, but it was fun.)

  • It’s close to 10 when we leave and go to Walmart and grab some oats. We drive to a duck pond. It’s 11ish by the time we get there. We walk around, try to figure out how to get the damn ducks to eat our food, and make out until 12ish.

  • We make out and talk until 1 or so.

What I liked was being able to change venues at my leisure in a natural way. It appeared both spontaneous and low-key.

KINO:

I’m not sure how necessary this is, but as far as I can recall, these are the moments and times I escalated, and specifically how I did it. This is lengthy, but I’m trying to be explicit for whoever this might help.

  • We hugged when we met.

  • When we were trying out the glasses, I was putting them on and taking them off of her.

  • I touched her arm and guided her with my hand on her lower back at times while we walked through the mall.

  • When we were walking out, I held her upper arm to guide her towards my car, then slipped my hand down her arm until we were holding hands.

  • When we got in my car, she was trying to adjust her seat. I leaned across her and spent a while trying to figure it out. I said, “this is my way of trying to touch you,” and it was funny.

  • I touched her jeans as we drove, and commented on how they didn’t feel like jeans. I kept rubbing them throughout the drive, and when I offered her a blanket, I said she could use it as long as I could keep touching her legs. Again, funny.

  • It was cold as we were feeding the ducks. I had her put on my sweater, and we hugged tightly as we walked around.

  • I actually didn’t want to kiss her on the first date, but she kept smiling, staring at my eyes, looking at my lips, and licking her lips. The main deterrent was that I had slightly dry lips, and didn’t want her to see me lick my lips. When I caught a chance to lick them subtly, I went in and kissed her.

  • We made out for a while outside, then for a while in my car. My hands naturally started roaming under her clothes. Once she moved my hand, and I backed off for a while. An hour later, she moved my hand again, and said she wasn’t ready, that it was too soon. I just kept kissing her and backed off. It was fine.

CONVERSATION:

I don’t have any specific phrases I think were magic, and I’m coming to think there is no such thing. I’m naturally light-hearted and have an easy time talking and joking around. I few things that I think were helpful with the conversation:

  • My mindset was healthy.

  • I tried to allow the conversation to become about emotion rather than simply facts. I also allowed for silence when it felt appropriate. At one point, she was talking about her family, and she said something like, “You probably don’t want to hear this.” I just softly said, “I do.” Later, she said that this is the thing that makes her saddest, and then paused as though she wasn’t sure whether to go on. I just looked at her and said nothing. She kept talking, and said she’s never told anyone this before. This was very intimate.

LESSONS:

  • I have the tendency to want to perform, to be an entertainer. Throughout the date, I spoke freely whatever I wanted to. I was very vulnerable, and the date was very intimate.

  • This honesty I believe worked because my mindset was healthy. By healthy, I mean that I was more curious about finding out about her than I was about making sure she liked me so I could feel validated. “For those who are single, dateless and stressing about it. Take a moment to consider……That instead of feeling the need to impress them, you could wonder if they impress you?” (http://markmanson.net/change-your-mind.) Something like that.

  • Logistics! Again, I sense that I suck at this. It took a hell of a lot of my time to figure out that feeding ducks really is okay. But getting it right, so that there were a number of different venues that felt natural, was pretty helpful I think. This is a skillset I need to develop.

HELP!

That date was on Monday. We are going out again on Friday. I feel confident in my ability to go about integrating her into my life if this goes well, but I am a little lost on this date. I want it to be fun and loose, but I don’t want it to be too similar to the last date.

Here are my ideas so far:

ComedySportz. - I like that it shakes things up and that it would be super fun. I don’t know how interactive it is, and I don’t know if the limited ability to talk would be a big deal. I also don’t like that it’s 2 hours. I’d rather spend an hour on something and move on whenever I’m ready.

Art museum. - I like that I can talk and touch. I feel like we’ve spent a good amount of time just talking though, and I’m wary of just walking around talking about things all the time.

Ice skating. - On paper this looks cool, but I’ve only ice skated once, and I’m not sure how fun that would be if I’m not competent. I also like the idea of doing something quirky she’s unlikely to have done much before, and I’m not sure this works for that. Also tough to see how it naturally segues into something else besides hot chocolate, which we’ve already done.

Dancing. - On paper this looks really cool too. But I don’t really want to do it.

Mini golf / bowling. - Too trite. I feel like I have to do something a little bigger since it’s a Friday night. I’m not sure that lowkey and predictable is the way to go here.

If I were forced to make a decision right now, I’d do something like this:

7:15 - meet up, find a reason to stop by my place, and give her the grand tour. Have her try a juice that I made or something.

7:45 - 10:00 - go to Comedy Sportz (an improv show).

10:00 - 10:30 - walk down the street and buy some horchata, since she has told me I need to try that. (Still have to find a horchata place there, but I can figure that out.

10:30 - If it’s clear and warm out, lay on a hill and see if we can identify constellations? I’m not sure. I get stuck at this point. I want something isolating but I don’t want to just hang out in my car, and I don’t feel comfortable in my apartment (roommates in the front room, and nothing to do in my room). Any ideas here?

Alternatively, I could do something like this:

730-830 - go to the museum of art and look around.

830-930 - get drinks at a juice bar or something. Stop by walmart and buy coloring books and crayons. Draw portraits of each other or something.

930-10 - head to the street the comedy club is on and walk around.

10-12 - go to the comedy club.

12-1 - take her to a look out point over the city where we have to finish our portraits.

I don’t know. As I’ve said, I’m trying to figure out this stuff without looking too try-hard. Part of the pressure I feel here is that I know she gets asked out a ton, and I want to set myself apart.

Shit, this got long.

TL;DR: - I had a great first date on Monday. The keys were having a mindset where I valued honesty over performance instead of seeking her validation, and having a strong but easy-going plan in place. Now, I’m trying to figure out what to do for a second date. This is something I struggle with, for whatever reason.

Any ideas, guys?